Trimethylsilyl iodide → HCID 18687842, compound

HRID 1873194Notes

Reaction equation

HRID 1873194 reaction equation
I[Si](C)(C)C.[Br:6][C:7]1[CH:30]=[C:29]([C:31]2[C:40]3[C:41]4[CH:47]=[CH:46][CH:45]=[CH:44][C:42]=4[S:43][C:39]=3[C:38]([Br:48])=[C:37]3[C:32]=2[CH:33]=[CH:34][CH:35]=[CH:36]3)[CH:28]=[C:27]([Br:49])[C:8]=1[O:9][CH:10]([P:19](=[O:26])([O:23]CC)[O:20]CC)[CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(Cl)Cl>[Br:6][C:7]1[CH:30]=[C:29]([C:31]2[C:40]3[C:41]4[CH:47]=[CH:46][CH:45]=[CH:44][C:42]=4[S:43][C:39]=3[C:38]([Br:48])=[C:37]3[C:32]=2[CH:33]=[CH:34][CH:35]=[CH:36]3)[CH:28]=[C:27]([Br:49])[C:8]=1[O:9][CH:10]([P:19](=[O:20])([OH:26])[OH:23])[CH2:11][CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 131721965HCID 131721965, compound

Product 1

HCID 18687842HCID 18687842, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Iodotrimethylsilane (0.56 mL, 3.93 mmol) was added dropwise to a stirred, 0° C. solution of {1-[2,6-dibromo-4-(6-bromo-benzo[b]naphtho[2,3-d]thiophen-11-yl)-phenoxy ]-3-phenyl-propyl}-phosphonic acid, diethyl ester (1.07 g, 1.31 mmol) in methylene chloride (26 mL) under a dry nitrogen atmosphere over a period of 10 min. After 1 h at 0° C., the reaction mixture was quenched with 10% aq sodium bisulfite (1 mL), stirred at ambient temperature for 30 min. The mixture was partitioned in methylene chloride (100 mL) and water (100 mL). The methylene chloride phase was washed with 18% aq HCl (100 mL), concentrated, and triturated with pet. ether to afford a crude solid (0.894 g). The solid was then recrystalized from 85% aq. acetic acid (50 mL) to provide the title compound as a off-white solid (0.466 g, 47%): NMR (CDCl3); δ8.33 (d, J=9 Hz, 1 H), 7.76 (d, J=7 Hz, 1 H), 7.59 (ddd, J=8, 7, 1 Hz, 1 H), 7.48-7.40 (m, 3 H), 7.36-7.28 (m, 2 H), 7.06-6.98 (m, 5 H), 6.91-6.83 (m, 1 H), 6.77 (d, J=8 Hz, 1 H), 5.47-5.42(m, 1 H), 4.50 (s, 2 H), 3.05-2.85 (m, 2 H), 2.59-2.41 (m, 2 H); MS (FAB-): [M-H]-, 3 bromine isotope pattern, 756; Anal. Calc. for C31H22Br3O4PS: C, 48.91, H, 2.91, N, 0.00. Found: C, 49.29, H, 2.90, N, -0.02.

Workup

  1. customthe reaction mixture was quenched with 10% aq sodium bisulfite (1 mL)
  2. customThe mixture was partitioned in methylene chloride (100 mL)
  3. washThe methylene chloride phase was washed with 18% aq HCl (100 mL)
  4. concentrationconcentrated
  5. customtriturated with pet. ether
  6. customto afford a crude solid (0.894 g)
  7. customThe solid was then recrystalized from 85% aq. acetic acid (50 mL)

Sources & evidence

ORD record
ord-103fceed3b0841d783d73943496eb19c
Source dataset
uspto-grants-2000_08
Patent number
US06110962

Reaction notes

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